6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosa­minide methanol monosolvate

Chen, B.; Guo, M.; Jin, W.-H.; Wang, Y.-W.; Liang, H.-Z.

doi:10.1107/S1600536810036238

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2561

doi:10.1107/S1600536810036238

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6-Methyl-2-pyridyl N-acetyl-1-thio-β-D-glucosaminide methanol monosolvate

Bo Chen,^a Miao Guo,^a Wei-Hua Jin,^a Yan-Wei Wang ^a and Hong-Ze Liang ^a ^*

^aFaculty of Materials Science and Chemical Engineering, Ningbo University, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: lianghongze@nbu.edu.cn

(Received 31 August 2010; accepted 9 September 2010; online 15 September 2010)

In the title compound, C₁₄H₂₀N₂O₅S·CH₄O, the pyranose and pyridine rings are linked through an S atom. The pyranose ring has a normal chair conformation. An intramolecular O—H⋯N hydrogen bond occurs. Intermolecular O—H⋯O, N—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of glucopyranosides, see: Ashry et al. (2006 ). For the structure of an α-D-glucosaminide, see: Harrison et al. (2007 ).

Experimental

Crystal data

C₁₄H₂₀N₂O₅S·CH₄O
M_r = 360.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3841 (15) Å
b = 14.041 (3) Å
c = 17.038 (4) Å
V = 1766.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.51 × 0.27 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.932, T_max = 0.950
12687 measured reflections
3173 independent reflections
2997 reflections with I > 2σ(I)
R_int = 0.161

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.170
S = 1.05
3173 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.70 e Å⁻³
Absolute structure: Flack (1983 ), 1334 Fiedel pairs
Flack parameter: 0.01 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.15	2.925 (4)	149
O2—H2A⋯O3ⁱⁱ	0.82	2.02	2.794 (3)	156
O3—H3A⋯O4ⁱⁱ	0.82	1.88	2.646 (3)	155
O4—H4A⋯O6ⁱⁱⁱ	0.82	1.82	2.637 (4)	176
O6—H6⋯N2	0.82	1.98	2.795 (4)	175
C8—H8A⋯O5^iv	0.93	2.48	3.329 (4)	151
C12—H12C⋯O1^v	0.96	2.58	3.520 (4)	165
C15—H15C⋯O3^vi	0.96	2.56	3.367 (5)	142
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (vi) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036238/xu5024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036238/xu5024Isup2.hkl

checkCIF report

Comment top

Thioglycosides are widely employed as biological inhibitors, glycosyl donors and enzyme resistant ligands for affinity chromatography (Ashry et al., 2006). Here we report the crystal structure of the title compound (Scheme 1). The title compound crystallizes exclusively as the β anomer. The molecule contains a pyranose ring and a pyridine ring linked by a sulfur atom. The pyranose ring has a normal chair conformation, similar to that found in an α-D-glucosaminide (Harrison et al. 2007). The extensive hydrogen bonding network is present in the crystal structure, involving O—H···O, O—H···N and N—H···O hydrogen bonding (Table 1). Weak intermolecular C—H···O hydrogen bonding is also present in the crystal structure.

Related literature top

For applications of glucopyranosides, see: Ashry et al. (2006). For the structure of an α-D-glucosaminide, see: Harrison et al. (2007).

Experimental top

6'-Methyl-2'-pyridyl-2,3,4,6-tetraacetyl-1-thio-β-D-glucosaminide (1.5 g, 3.3 mmol) was dissolved in MeOH (10 ml) and one equivalent MeONa was added. The process of deacetylation was monitored by ¹H NMR. After removal of the solvent, the solid residue was washed with ethanol and ether, and then crystallized from H₂O/MeOH to give the title compound (0.23 g) as colorless crystals.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I) showing the labeling of the non-H atoms and 50% probability ellipsoids. Dashed line indicates the hydrogen bonding.

6-Methyl-2-pyridyl N-acetyl-1-thio-β-D-glucosaminide methanol monosolvate top

Crystal data top

C₁₄H₂₀N₂O₅S·CH₄O	F(000) = 768
M_r = 360.42	D_x = 1.355 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12040 reflections
a = 7.3841 (15) Å	θ = 1.9–24.5°
b = 14.041 (3) Å	µ = 0.22 mm⁻¹
c = 17.038 (4) Å	T = 296 K
V = 1766.5 (6) Å³	Block, colourless
Z = 4	0.51 × 0.27 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3173 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.161
Detector resolution: 0 pixels mm^-1	θ_max = 25.2°, θ_min = 1.9°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −16→16
T_min = 0.932, T_max = 0.950	l = −20→20
12687 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.1077P)² + 0.760P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
3173 reflections	Δρ_max = 0.56 e Å⁻³
222 parameters	Δρ_min = −0.70 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1334 Fiedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (12)

Crystal data top

C₁₄H₂₀N₂O₅S·CH₄O	V = 1766.5 (6) Å³
M_r = 360.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3841 (15) Å	µ = 0.22 mm⁻¹
b = 14.041 (3) Å	T = 296 K
c = 17.038 (4) Å	0.51 × 0.27 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3173 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2997 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.950	R_int = 0.161
12687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.170	Δρ_max = 0.56 e Å⁻³
S = 1.05	Δρ_min = −0.70 e Å⁻³
3173 reflections	Absolute structure: Flack (1983), 1334 Fiedel pairs
222 parameters	Absolute structure parameter: 0.01 (12)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.80502 (12)	0.14422 (6)	0.34312 (4)	0.0246 (2)
O1	0.6461 (3)	0.24215 (17)	0.23124 (11)	0.0209 (5)
O2	0.3258 (3)	0.26631 (17)	0.13049 (12)	0.0238 (5)
H2A	0.3087	0.2660	0.0829	0.036*
O3	0.7290 (3)	0.28865 (18)	0.02141 (12)	0.0243 (5)
H3A	0.6376	0.3204	0.0135	0.036*
O4	0.9501 (3)	0.12909 (17)	0.04864 (13)	0.0237 (5)
H4A	0.8695	0.0906	0.0392	0.036*
O5	1.0621 (4)	−0.03011 (17)	0.24234 (16)	0.0327 (6)
O6	0.8051 (4)	−0.00609 (19)	0.51072 (18)	0.0449 (8)
H6	0.7982	0.0517	0.5048	0.067*
N1	1.0936 (4)	0.1246 (2)	0.20602 (15)	0.0221 (6)
H1A	1.1689	0.1711	0.2024	0.027*
N2	0.8034 (4)	0.1914 (2)	0.49004 (14)	0.0232 (6)
C1	0.8218 (5)	0.2112 (2)	0.25267 (16)	0.0205 (6)
H1B	0.9010	0.2665	0.2604	0.025*
C2	0.9047 (4)	0.1441 (2)	0.19007 (17)	0.0191 (6)
H2C	0.8369	0.0841	0.1891	0.023*
C3	0.8913 (4)	0.1928 (2)	0.10900 (16)	0.0179 (6)
H3B	0.9773	0.2460	0.1096	0.021*
C4	0.7073 (4)	0.2349 (2)	0.09201 (15)	0.0186 (6)
H4B	0.6190	0.1837	0.0837	0.022*
C5	0.6461 (4)	0.2985 (2)	0.15999 (16)	0.0189 (6)
H5A	0.7311	0.3516	0.1658	0.023*
C6	0.4550 (4)	0.3376 (2)	0.14950 (17)	0.0211 (7)
H6A	0.4181	0.3690	0.1976	0.025*
H6B	0.4562	0.3850	0.1081	0.025*
C7	0.8079 (5)	0.2318 (2)	0.41830 (17)	0.0220 (7)
C8	0.8187 (5)	0.3293 (2)	0.40626 (18)	0.0272 (7)
H8A	0.8197	0.3549	0.3559	0.033*
C9	0.8281 (6)	0.3875 (3)	0.4726 (2)	0.0360 (9)
H9A	0.8383	0.4532	0.4671	0.043*
C10	0.8221 (5)	0.3470 (3)	0.5465 (2)	0.0343 (8)
H10A	0.8265	0.3853	0.5910	0.041*
C11	0.8095 (5)	0.2491 (3)	0.55384 (17)	0.0268 (7)
C12	0.8040 (6)	0.2002 (3)	0.63295 (18)	0.0342 (8)
H12A	0.7956	0.1326	0.6255	0.051*
H12B	0.7005	0.2221	0.6619	0.051*
H12C	0.9123	0.2149	0.6616	0.051*
C13	1.1595 (5)	0.0380 (2)	0.22624 (18)	0.0258 (8)
C14	1.3633 (5)	0.0325 (3)	0.2284 (2)	0.0370 (9)
H14A	1.3997	−0.0307	0.2431	0.055*
H14B	1.4089	0.0773	0.2661	0.055*
H14C	1.4111	0.0473	0.1775	0.055*
C15	0.9488 (6)	−0.0426 (3)	0.4639 (3)	0.0419 (10)
H15A	1.0311	0.0080	0.4511	0.063*
H15B	0.9002	−0.0691	0.4164	0.063*
H15C	1.0120	−0.0912	0.4925	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0396 (5)	0.0254 (4)	0.0087 (4)	−0.0002 (4)	−0.0009 (3)	0.0015 (3)
O1	0.0240 (12)	0.0320 (12)	0.0068 (9)	0.0013 (9)	0.0010 (8)	0.0021 (9)
O2	0.0240 (11)	0.0350 (12)	0.0124 (10)	−0.0047 (10)	−0.0019 (9)	0.0012 (9)
O3	0.0243 (12)	0.0387 (14)	0.0100 (10)	0.0057 (11)	0.0008 (8)	0.0050 (9)
O4	0.0247 (11)	0.0313 (12)	0.0150 (10)	0.0001 (10)	0.0048 (9)	−0.0054 (9)
O5	0.0398 (15)	0.0250 (13)	0.0333 (14)	0.0013 (11)	0.0009 (12)	0.0023 (11)
O6	0.0568 (19)	0.0269 (13)	0.0509 (17)	0.0004 (15)	0.0235 (16)	0.0076 (12)
N1	0.0221 (14)	0.0258 (14)	0.0184 (13)	−0.0009 (11)	−0.0029 (11)	0.0024 (11)
N2	0.0258 (14)	0.0322 (15)	0.0117 (12)	0.0010 (13)	−0.0009 (11)	0.0008 (10)
C1	0.0252 (15)	0.0290 (16)	0.0073 (12)	0.0010 (14)	0.0000 (12)	−0.0004 (12)
C2	0.0237 (15)	0.0215 (15)	0.0120 (13)	−0.0002 (13)	0.0007 (11)	0.0014 (12)
C3	0.0224 (15)	0.0246 (16)	0.0068 (13)	−0.0012 (12)	0.0020 (12)	−0.0024 (12)
C4	0.0223 (16)	0.0270 (16)	0.0064 (13)	−0.0029 (13)	0.0026 (11)	−0.0002 (11)
C5	0.0271 (16)	0.0219 (14)	0.0078 (13)	−0.0031 (13)	0.0002 (11)	0.0009 (12)
C6	0.0238 (16)	0.0288 (16)	0.0107 (13)	−0.0020 (13)	−0.0010 (12)	−0.0013 (12)
C7	0.0218 (15)	0.0331 (17)	0.0111 (13)	0.0014 (15)	0.0003 (12)	−0.0026 (12)
C8	0.0349 (18)	0.0301 (17)	0.0167 (15)	0.0039 (15)	0.0015 (15)	0.0009 (12)
C9	0.045 (2)	0.0299 (18)	0.0335 (19)	0.0033 (17)	0.0035 (18)	−0.0029 (15)
C10	0.0397 (19)	0.041 (2)	0.0221 (16)	0.0042 (18)	0.0008 (16)	−0.0115 (15)
C11	0.0231 (15)	0.045 (2)	0.0124 (14)	0.0043 (15)	−0.0010 (13)	−0.0036 (14)
C12	0.042 (2)	0.052 (2)	0.0090 (14)	0.0022 (19)	−0.0021 (15)	−0.0020 (14)
C13	0.039 (2)	0.0228 (16)	0.0155 (14)	0.0028 (15)	−0.0014 (14)	−0.0017 (12)
C14	0.036 (2)	0.034 (2)	0.041 (2)	0.0059 (16)	−0.0039 (17)	0.0026 (16)
C15	0.035 (2)	0.037 (2)	0.054 (3)	0.0018 (18)	0.009 (2)	0.0094 (19)

Geometric parameters (Å, º) top

S1—C7	1.776 (3)	C4—C5	1.531 (4)
S1—C1	1.810 (3)	C4—H4B	0.9800
O1—C1	1.416 (4)	C5—C6	1.524 (4)
O1—C5	1.449 (3)	C5—H5A	0.9800
O2—C6	1.420 (4)	C6—H6A	0.9700
O2—H2A	0.8200	C6—H6B	0.9700
O3—C4	1.429 (3)	C7—C8	1.386 (5)
O3—H3A	0.8200	C8—C9	1.397 (5)
O4—C3	1.431 (4)	C8—H8A	0.9300
O4—H4A	0.8200	C9—C10	1.382 (5)
O5—C13	1.227 (4)	C9—H9A	0.9300
O6—C15	1.423 (5)	C10—C11	1.383 (5)
O6—H6	0.8200	C10—H10A	0.9300
N1—C13	1.355 (4)	C11—C12	1.513 (4)
N1—C2	1.447 (4)	C12—H12A	0.9600
N1—H1A	0.8600	C12—H12B	0.9600
N2—C7	1.348 (4)	C12—H12C	0.9600
N2—C11	1.357 (4)	C13—C14	1.507 (6)
C1—C2	1.550 (4)	C14—H14A	0.9600
C1—H1B	0.9800	C14—H14B	0.9600
C2—C3	1.545 (4)	C14—H14C	0.9600
C2—H2C	0.9800	C15—H15A	0.9600
C3—C4	1.510 (5)	C15—H15B	0.9600
C3—H3B	0.9800	C15—H15C	0.9600

C7—S1—C1	104.68 (15)	O2—C6—H6A	108.9
C1—O1—C5	112.5 (2)	C5—C6—H6A	108.9
C6—O2—H2A	109.5	O2—C6—H6B	108.9
C4—O3—H3A	109.5	C5—C6—H6B	108.9
C3—O4—H4A	109.5	H6A—C6—H6B	107.7
C15—O6—H6	109.5	N2—C7—C8	123.4 (3)
C13—N1—C2	124.3 (3)	N2—C7—S1	111.3 (2)
C13—N1—H1A	117.9	C8—C7—S1	125.3 (2)
C2—N1—H1A	117.9	C7—C8—C9	117.5 (3)
C7—N2—C11	118.3 (3)	C7—C8—H8A	121.3
O1—C1—C2	111.8 (2)	C9—C8—H8A	121.3
O1—C1—S1	108.4 (2)	C10—C9—C8	119.6 (3)
C2—C1—S1	107.3 (2)	C10—C9—H9A	120.2
O1—C1—H1B	109.8	C8—C9—H9A	120.2
C2—C1—H1B	109.8	C9—C10—C11	119.5 (3)
S1—C1—H1B	109.8	C9—C10—H10A	120.2
N1—C2—C3	108.2 (2)	C11—C10—H10A	120.2
N1—C2—C1	111.5 (3)	N2—C11—C10	121.6 (3)
C3—C2—C1	108.7 (2)	N2—C11—C12	116.2 (3)
N1—C2—H2C	109.5	C10—C11—C12	122.2 (3)
C3—C2—H2C	109.5	C11—C12—H12A	109.5
C1—C2—H2C	109.5	C11—C12—H12B	109.5
O4—C3—C4	112.3 (2)	H12A—C12—H12B	109.5
O4—C3—C2	110.2 (2)	C11—C12—H12C	109.5
C4—C3—C2	113.7 (2)	H12A—C12—H12C	109.5
O4—C3—H3B	106.7	H12B—C12—H12C	109.5
C4—C3—H3B	106.7	O5—C13—N1	123.1 (3)
C2—C3—H3B	106.7	O5—C13—C14	122.6 (3)
O3—C4—C3	105.5 (2)	N1—C13—C14	114.3 (3)
O3—C4—C5	111.2 (2)	C13—C14—H14A	109.5
C3—C4—C5	110.4 (2)	C13—C14—H14B	109.5
O3—C4—H4B	109.9	H14A—C14—H14B	109.5
C3—C4—H4B	109.9	C13—C14—H14C	109.5
C5—C4—H4B	109.9	H14A—C14—H14C	109.5
O1—C5—C6	107.1 (2)	H14B—C14—H14C	109.5
O1—C5—C4	108.3 (2)	O6—C15—H15A	109.5
C6—C5—C4	113.2 (3)	O6—C15—H15B	109.5
O1—C5—H5A	109.3	H15A—C15—H15B	109.5
C6—C5—H5A	109.3	O6—C15—H15C	109.5
C4—C5—H5A	109.3	H15A—C15—H15C	109.5
O2—C6—C5	113.3 (3)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.15	2.925 (4)	149
O2—H2A···O3ⁱⁱ	0.82	2.02	2.794 (3)	156
O3—H3A···O4ⁱⁱ	0.82	1.88	2.646 (3)	155
O4—H4A···O6ⁱⁱⁱ	0.82	1.82	2.637 (4)	176
O6—H6···N2	0.82	1.98	2.795 (4)	175
C8—H8A···O5^iv	0.93	2.48	3.329 (4)	151
C12—H12C···O1^v	0.96	2.58	3.520 (4)	165
C15—H15C···O3^vi	0.96	2.56	3.367 (5)	142

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z; (iii) −x+3/2, −y, z−1/2; (iv) −x+2, y+1/2, −z+1/2; (v) x+1/2, −y+1/2, −z+1; (vi) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂O₅S·CH₄O
M_r	360.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.3841 (15), 14.041 (3), 17.038 (4)
V (Å³)	1766.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.51 × 0.27 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.932, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	12687, 3173, 2997
R_int	0.161
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.170, 1.05
No. of reflections	3173
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.70
Absolute structure	Flack (1983), 1334 Fiedel pairs
Absolute structure parameter	0.01 (12)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.15	2.925 (4)	149
O2—H2A···O3ⁱⁱ	0.82	2.02	2.794 (3)	156
O3—H3A···O4ⁱⁱ	0.82	1.88	2.646 (3)	155
O4—H4A···O6ⁱⁱⁱ	0.82	1.82	2.637 (4)	176
O6—H6···N2	0.82	1.98	2.795 (4)	175
C8—H8A···O5^iv	0.93	2.48	3.329 (4)	151
C12—H12C···O1^v	0.96	2.58	3.520 (4)	165
C15—H15C···O3^vi	0.96	2.56	3.367 (5)	142

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z; (iii) −x+3/2, −y, z−1/2; (iv) −x+2, y+1/2, −z+1/2; (v) x+1/2, −y+1/2, −z+1; (vi) −x+2, y−1/2, −z+1/2.

Acknowledgements

This project was sponsored by the Cultivation Program of Young and Middle-aged Academic Leaders in Zhejiang Higher Education Institutions, the Natural Science Foundation of Ningbo City (Nos. 2009 A610047 and 2010 A610027) and the K. C. Wong Magna Fund of Ningbo University. We thank Professor X. Li for help with the structural analysis.

References

Ashry, E. S. H., Awad, L. F. & Atta, A. I. (2006). Tetrahedron, 62, 2943–2998. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harrison, W. T. A., Yathirajan, H. S., Narayana, B., Sreevidya, T. V. & Sarojini, B. K. (2007). Acta Cryst. E63, o3248. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar